The first time I listened to the Hold Steady, I was committing low-level health insurance fraud and mopping a floor in a hotel on an island 10 miles off the coast of New Hampshire.

Now, when I say “listened,” I mean really listened. Not just heard, since I know I must have heard the Hold Steady before — the music was playing on an old iPod that my college friends had filled with their favorite albums and given to me earlier that year. My friends were cooler than me, which would always be true at any time in my life. (I tend to punch above my weight when it comes to friendship.) After my buddy Josh got a new iPod Mini, they gifted me his old, clunky white one, deciding once and for all that I needed to learn about music, because I barely knew anything and man was it breaking their hearts.

I had always been music-dumb. While I liked listening to it just fine, my tastes were completely haphazard, a grab bag of every random tune fate had thrown my way. I had tapes I’d gotten when I was a kid — the White Album, Appetite for Destruction — which my half-brother had made for me by holding a recorder to his father's record player. I listened to 107.3 WAAF, the only station I could get on my alarm clock radio, the cheesy post-grunge drowning out my parents' fighting. The only CDs I owned were Silverchair’s Frogstomp and the Goo Goo Dolls’ A Boy Named Goo, both of which I’d stolen from the brand new Walmart in the next town over. Unfortunately, I hadn’t bothered to steal a CD player, which made being able to listen to the albums rather hard.

By the time I got to college, I still had the CDs, plus a random array of MP3s on my hand-me-down laptop. I listened to music but never embraced it — I didn’t hide my ignorance, but I didn’t seek out anything new, either. Of course, this drove my friends insane. They didn’t want me to just consume music like junk food, like something that could be anything, as long as it got the job done. They cared about music and wanted me to care too. I think they must have decided to give me Josh’s old iPod the day one of them, Big Pete, saw me lugging my giant, weighty laptop around in my backpack with a headphones cord snaking out of the zipper.

I listened to music but never embraced it — I didn’t hide my ignorance, but I didn’t seek out anything new, either.

“Isaac,” Pete said, with dawning horror. “Have you been carrying around your laptop all day just to listen to your shitty MP3s?”

“…Yes?” I said.

Fast-forward to the island off the coast of New Hampshire, to mopping the floor, to the impending insurance fraud, to really listening to the Hold Steady for the first time. The name of the album was Separation Sunday, and every song seemed to be sung right to me. How else could I have recognized so much of it? The low-level drug dealing, the accusatory hood rat friends, the ER visits. Drinking gin from jam jars.

Separation Sunday was the kind of rock ’n’ roll I’d been missing. Music that felt like an anthem crossed with a fistfight, a guided free fall — loud and cutting, but built with purpose. The singer sounded brash, both couldn’t-give-two-shits and passionate in turns. Sometimes he’d twist his voice into something approaching tunefulness, even beauty, then throw it all away to snarl, mutter, and shout. It was riveting.

I could see my past and experiences in the songs. My friends. Not the ones from college, so kind and generous with their iPods, but the ones back home, from a town called “Hostile, Massachusetts” (a song I didn’t know yet because my buddies hadn’t put Almost Killed Me, the Hold Steady’s first album, on the iPod). The characters in Separation Sunday — Holly and Charlemagne and Gideon — felt familiar. They were the people I grew up with; they were me. There were also plenty of references to Jesus and churches, enough that I started to wonder if my friends had snuck a Christian rock band onto the iPod as a joke. But fuck it, I decided. If this was Christian rock, then, I guess, I was into Christian rock now.

On the island, my job was mostly custodial with a little maintenance work. Not exactly what my parents were hoping I'd be doing after graduating from college and passing up an opportunity at the Department of Justice in Washington, DC. It was late in the summer, and I had come to the island to help with the last few hotel guests and then close all the buildings down for the season. It was a dependable job, one I'd been working on and off since I was 16.

I had arrived on the island the night before. When I got off the ferry, I was immediately greeted by friends. We did what friends working on an island do. We drank, and we drank some more, and eventually we ended up stealing a boat. Which we would argue was more like borrowing, since we fully intended to return it when we were done. It was a small thing, a metal skiff, meant to get a few folks from island to island when the rowboats wouldn't do. Nothing like the fine sailboats rich vacationers would moor in the harbor.

Jonny, one of my buddies, sat at the engine, steering us out past the breakwater and into open ocean. I was drunk and bold and had absolutely no idea what I was going to do with the rest of my life but overjoyed to be back north after a brutal August in Washington. I stood at the bow, hands wrapped around a rope, laughing as our metal skiff bounced off the waves — which, as my buddy Dave pointed out, were pretty choppy tonight and maybe it’d be best if I sat down. Not to mention the water had made the metal slippery and my cowboy boots weren't helping any.

I don't remember my face bouncing off the bow of the boat, or falling backward, or my friends cutting the engine. I was just looking at the ocean one minute and the next, I was staring up at the stars, my back damp, somehow flush with the bottom of the boat. I sat up and felt blood warming my mouth and the front of my shirt. Jonny asked if I was okay and I smiled at the absurdity of the question.

"Fuck, man,” said Dave. My front tooth, which was already fake thanks to a fight with a redheaded kid named Paul in the fourth grade, was gone, leaving behind a black, blood-edged hole.

Under the full moon, we searched the murky water at the bottom of the boat for my tooth and couldn’t find a damn thing. Finally, we gave up and decided this was perhaps a sign to head for shore. Jonny gunned the engine. Slowly, the skiff crept back toward the dock.

The general consensus was that I should hide the injury until the next day. While staff didn’t get official health insurance, there was a pool of money we all paid into that was used to cover on-the-job injuries, should they arise (which they inevitably did). I’d been paying into that pool since I was 16. As for the fact that I wasn’t at work when I got hurt — rather, I had been drunk on a stolen boat — that just seemed like a technicality.

I could see my past and experiences in the songs.

The next day, hungover and mopping a hardwood floor in a room where guests had performed a talent show the night before, having shoved my bloody shirt into a compost bin and kept my gappy mouth shut at breakfast, deep in the throes of falling in love with Separation Sunday (although maybe I’d have to check on the whole “is this Christian” thing) and not just the album but also the band itself, a band that would become that rarity for musically challenged me — a band that I followed and whose albums I’d seek out, who I would even see live despite my never going to shows (a hang-up from growing up poor in a rural town, because who’d want to buy a ticket that cost more than three CDs and who the fuck could even get you to the venue anyhow?) — I listened to the album on repeat and as “Cattle and the Creeping Things” kicked into high gear and my manager was nowhere to be seen, I thought, This is it, and knocked over the bucket and threw myself down on the floor as hard as I could, my body starfished and prone, brown mop water seeping into my clothes.

My manager ran in. “Oh my god! What happened?”

"I don't know. I must have slipped," I said, actually a little dazed. (I might have overdone the throwing myself to the floor bit.)

"Isaac! Your mouth!"

I remembered the plan and flashed more of my remaining teeth, feigning shock as my hand went to my face.

"Wait, where is it?" my manager asked.

"What?"

"The tooth," she said, looking down at the floor. "Where'd it go?"

"Oh, man... I fell pretty hard... It must have..." I fumbled, my brain completely cobwebbed from the night before. "... Broken into a million pieces?"

My manager looked at me, her face scrunched. She weighed the bullshitness of my story against my very impressive pratfall plus the pain in the ass it’d be to deal with me further. “Fine,” she said.

From my headphones came the voice of Craig Finn, whose name I didn’t even know yet, singing, “You came into the party with a long black shawl,” as I picked the iPod off the floor and went to fill out an incident report in exchange for a new fake tooth.

A few years after the tooth incident, I found myself working at a bar in San Francisco. I had traded the Atlantic for the Pacific after leaving a couple jobs I shouldn't have left and being fired from some jobs that definitely should have fired me. The bar, which had been a legendary biker bar and before that a legendary gay bar, had a stellar jukebox and was open from 9 a.m. to 2 a.m. every day. It was the kind of workplace where I got reprimanded for smiling too much, or being nice to customers. There was a memorial wall with photos of bar employees who had died — like Steve, who couldn’t beat cancer for the second time, and the old owner, Hans, who was killed in an unsolved double murder. I was in my twenties, so I romanticized ending up on that wall someday. (If I’m being honest, I still do.)

Jef with one f manned the grill in the bar’s kitchen and was one of the coolest coworkers I’ve ever had. He was covered in tattoos — on his forearm was a candle burning at both ends, the emblem of hard partiers who get shit done. He was more comfortable in his skin than anyone else I'd ever met, a mishmash of Midwestern sports fan who loved baseball even more than he loved getting fucked up mixed with a punk rocker who was passionate about music writing. Jef wrote constantly about the shows he went to, in town and at festivals like South by Southwest. He kept it pretty quiet, but later in our friendship when he finally told me he was a writer, I’d always look for his stuff online. Though I usually didn’t know what bands or venues he was talking about, I read on for the pleasure of recognizing Jef’s idiosyncratic voice.

He was gay, often called me faggot, and liked to fuck with my New England sensibilities just to watch me squirm. “It's okay, I can say that word. You can't, but I can,” he’d tell me. Then, with a grin: “Not yet you can't, at least.”

We’d drink until we felt comfortable talking about all the darker things, the bad memories we tried not to keep. And then we'd drink some more, to keep us from remembering what was said the next day, nodding to each other at work before starting it all over again. We’d go to baseball games and ride our bikes together, day-drinking as we moved through the city with more swiftness and grace than we had any right to. Even if our legs wobbled and our balance was so shitty that barstools were not to be trusted, once we were up on two wheels everything was steady and smooth, as if our bikes were the better part of us. Jef rode everywhere. We all did.

The songs Craig Finn wrote were our stories, only better, and what more does one want from art but hope?

“You wanna just play the Hold Steady?” Jef would ask from the kitchen, while I cleaned the bar before the evening crowd showed up. Then he'd switch the music and turn it up loud. It was 2007 and the Hold Steady had come out with Almost Killed Me (2004), Separation Sunday (2005), Boy and Girls in America (2006), and would release Stay Positive the following year.

Like my college friends, Jef tried to teach me about the music he loved so much, surprised and amused by my ignorance. One time I asked him about the meaning of the letters “LFTR PLLR,” which were tattooed on his knuckles.

"Wait,” Jef said. “Let me get this straight. You love the Hold Steady?"

"Of course."

"But you have NO IDEA who Lifter Puller are?"

"No. Never heard of ’em," I said. There was a pause and then I mumbled my usual, “I'm not great at music.”

“Come here,” he said, motioning toward the jukebox. “I want to play you something.”

Before Craig Finn was the lead singer of the Hold Steady, he was in Lifter Puller, along with Hold Steady bandmate Tad Kubler, from around 1994 to 2000. For all that time, and the first few years of the Hold Steady, Craig Finn had had a day job; he didn’t get to devote his time fully to music until he was 33 or 34. Jef and I liked that. Jef was 10 years older than me, and a year or two younger than Finn. It made us feel like we could start working on our dreams tomorrow.

“He's spent some time in Boston, think he might have even been born there, like you,” Jef told me. “But he's hardcore Minnesota, like me.”

I can't remember if Jef was raised Catholic, but Finn and I were, which explained the religious themes in his lyrics. And it was amazing to see Finn taking the world he knew and making art out of it. The band’s music was attainable in a way we’d never been taught to expect. The songs operated as mirrors, reflecting our own experiences back onto us, even as they were windows, showing us how art could be made from the stuff of our lives — a world of misdemeanors and half-hearted escapism, through which real escape might be possible. The songs Craig Finn wrote were our stories, only better, and what more does one want from art but hope?

Patrick Costello / Courtesy Self-Starter Foundation

Lifter Puller

One day at work Jef turned to me and asked, “Wanna go see the Hold Steady tonight?”

I didn’t even blink. “Hell yes!”

“Slow down,” he said. “I can’t go with you, I’ve gotta work. Plus I already went last night. Wait, did you not know they were in town?”

I tried to pretend my feelings weren’t hurt.

“Oh, chin up, buttercup, I figured you knew. Here's the deal. I'm writing up the show, but I forgot to bring my camera last night, so I need you to go snap some pics tonight. Think you can do that?”

He held out a ticket and a backstage pass to the Fillmore. The paper shone in the harsh, greasy light of the bar's kitchen.

“Wait,” I said. “You write? I didn't know that.”

“Bitch, there's so much you don't know about me it could fill AT&T Park. You in or not?”

I went home from the bar and got my leather jacket, the one nice thing I owned, which I’d bought at the Levi's headquarters store in Union Square in the middle of a bender, the only time I really felt comfortable spending money on myself. I’d been bright-eyed and exhausted, trying to charm the salespeople, who probably didn’t care whether I purchased the $400 jacket or not and just wanted me the hell out of the store. I had bought it because the leather was rich and brown and it fit my awkward body like nothing before ever had.

I peeled the backstage pass sticker from its backing and stuck it to the front of my jacket. Only later did I notice that everyone else had kept theirs hidden and just flashed it when necessary.

If there's one thing I understood less than music, it was photography, but Jef had told me to get good shots of Craig, and I figured the closer I was, the better the shots would be. I squeezed my way forward until I was almost standing at Craig Finn's feet. Surrounding him were Tad Kubler on guitar, Galen Polivka on bass, Bobby Drake on drums, and Franz Nicolay on keyboards.

I was surprised to see Finn wearing a button-up shirt, a Grateful Dead dancing bear sticker on his baby blue guitar. He looked more suburban than I had expected, and it made me love him all the more. Here was a guy playing to a packed house at The Fillmore in San Francisco, and he looked like he had just dropped out of college and was surprised to find himself onstage.

The dust floated in the spotlights, as Craig Finn sang about dust floating in the spotlights.

Most of the people there looked more like Finn than Franz Nicolay, who was the stylish, sharp-dressed one of the group. I was covered in sweat, both my own and everyone else’s. The largely male audience — so emotional yet unaccustomed to displaying emotion — crushed up against me. Our bodies lifted one another up, and the physical sensation was a strange cross between fighting and hugging — minus anger, plus a crowd. The dust floated in the spotlights, as Craig Finn sang about dust floating in the spotlights.

That was the night I got it — the point of going to a live show. And for every feeling you could have at a show, well, there’s a Hold Steady lyric for that. We all sang along at the top of our lungs, Jef's camera dangling against my side as I got caught up in the music.

After I got home, sweaty and beer-filled, I peeled the backstage pass off my leather jacket. I never did get up the courage to go meet the band, but it was enough just to have had the chance. I stuck the pass on my bedroom mirror to make sure I saw it every day, a reminder that music and art and writing could take you out of your world and into another, even if only for a night.

The next morning, I was nursing a hangover that had crept over me like a heavy veil despite my attempt to thwart it by not sleeping. It was early in the morning, and the bar kitchen had just opened. I handed the camera back to Jef, who began clicking through the thumbnails right away.

“Isaac!” he yelled.

Immediately I thought I'd fucked up.

“Did you know you took over 700 pictures? Jesus. I didn't even know it could hold this many.” Jef started laughing, still looking through the photos. “Don't quit your day job, man. Half of these are of your feet. But I'll find something.”

Years passed and I was no longer working at the bar, though I still tried to get back as often as I could. Jef was working at a few other places around town. Like anyone who’s been in the service industry for a while, we were regulars at a bunch of spots — our new bars, our old bars, our friends’ bars.

Eventually I got a job that kept normal hours, with real health insurance, even. The office was cramped and the work could be frustrating, but I poured my heart into it. My twenties were dwindling.

On the day I can’t forget because I can’t redo it, I took a phone call outside on the sidewalk. It was a sunny and hot July afternoon in San Francisco. I know the phone call was important — or more accurately, that I must have thought it was important — but today I couldn't tell you a single thing about it.

Someone said my name and I turned around.

Right away I knew something was off, because Jef wasn't riding his bike. Instead, he was walking it slowly down the sidewalk, leaning on it like a crutch.

“Isaac,” he repeated.

It was early in the afternoon.

“Isaac. Fuck you.”

It was so beautiful out.

“Isaac. Isaac. Get the fuck off the phone. Let's go to the 500 Club.”

While I pretended to listen to the person on the other end of the line, my ears strained to turn each slurred sound Jef made into the word it wanted to be. Every word not even a word, but an inkblot of a word. I made the “cut it out” motion at him, my finger slicing my neck. My eyes flashing hot for a moment. I smiled, but it was strained.

He wouldn’t leave, so I considered pushing him a little, something playful to get him off my back, but thought better of it. Swaying against his bike, Jef barely had the edge over gravity as it was.

“Fuck you, man,” he said.

I plugged my finger into my ear and turned away, concentrating on the call. “What's that?” I asked the person I can't remember.

“Blow me,” said the person I'll never forget.

As Jef walked away, he flipped me off with both hands behind his back, his bike perched neatly on his hip, never falling. A perfect feat of fuck you pulled off with panache and grace, all from a guy who’d just been staggering a second ago.

It’s not that I could have saved Jef. I've lost enough people to know that.

They found Jef in his bedroom at the end of the week. It was July 4th. The reason for his death felt like a non-answer: booze, partying, who knows. We gathered at the bar and put his picture up on the wall with all the others. Our family, our cemetery. We played the music Jef loved so much and played it loud. I couldn’t bring myself to tell anyone about seeing him a few days earlier.

Six months later I left San Francisco for Brooklyn. The reasons seemed simple: There was a job. And San Francisco had changed, the way San Francisco always does. It's a boom-and-bust town, and yet another tech gold rush had taken hold, one that seemed much more entrenched than the last.

But I'd be lying if I said it wasn't other things too. Going to my favorite bar, watching more and more friends go up on the wall. Walking that same block every day, regretting the dumb, douchebaggy finger I’d stuck in my ear as I turned my back.

It’s not that I could have saved Jef. I've lost enough people to know that. You can't save someone when they're really going for it. That's like thinking I could have saved Steve, if only I'd just really put my mind to finding a cure for cancer. My sadness is purely selfish: I could have hung up that phone and spent a few more hours or days (depending on how high we could stay) with my friend. We could have laughed together some more while Jef gave me shit. He would have smiled at me in his way that always made me feel loved, that made me feel like we were in it together even though we had no idea what “it” was.

We could have gone to a baseball game.

Al Pereira / WireImage

Craig Finn & the We All Want the Same Things Band perform at their album release party at City Winery on April 4 in New York City.

I hadn’t known that Craig Finn was releasing solo albums until a friend told me about We All Want the Same Things, which came out earlier this year (though, true to form, I was heinously late to the Craig Finn solo album party, given that he’d put out his first in 2012). The album is beautiful in just the way I like, honest yet heightened, the mundane stuff of life transformed into storytelling. Everything busted and everyone trying their best. In one of my favorite songs on the album, “God in Chicago,” Finn doesn't even bother singing. He just tells a story full of petty crime and stepped-on drugs and sadness. Two people pressing up against each other. Money that doesn't really amount to much — but it does for them.

I’ve listened to this song again and again. It’s a song that makes me cry, even though I can barely describe why, which of course makes me think about Jef who almost certainly could have. I wonder what he would think of Finn’s solo work; I wish he could explain these records to me the way no one else could. How would Jef have grown over the years, developed as a writer? Would he have been able to write about these albums in a way that reached people, that got to the heart of what was worthy and wonderful about them?

It’s a song that makes me cry, even though I can barely describe why, which of course makes me think about Jef who almost certainly could have.

Actually, I know the answer to that last question. Absolutely. Sure, Jef would have been critical, because he never liked giving anyone a pass. But I like to think he would have enjoyed the new characters, would have movingly been able to illustrate the greater significance of Craig's stories, tackling things like PTSD and the opioid epidemic.

In the Hold Steady song “Stevie Nix,” Craig Finn sang, “Lord, to be 33 forever,” which I recognize as another one of those Christian references that made me so suspicious all those years ago but also as a pleasantly comfortable age to want to be, weirdly attainable in a landscape of rock that’s all about 16, 17, 18, 27 at the most. But I can’t even do that — I’m 34 now. I’ve grown up with Craig Finn’s voice in my ears. I’m pretty sure I know where his albums end and my life begins, but I’m grateful that he so often blurs the line. That his music makes me feel like me and my friends live right there in those songs.

Just the other day I saw some of my college buddies. The ones who were so freaked out by my musical ignorance that they gave me Josh’s iPod full of albums all those years ago, still one of the best gifts anyone has ever gotten me. Josh and his wife and their beautiful baby are moving to Los Angeles, so we got together for a going-away party. We’re all over the place these days, but a bunch of us made it, up from DC and down from Massachusetts. Big Pete didn’t show because he’s about 13 hours west of Nairobi doing aid work, but word is he’ll visit this summer.

And me? I still visit Jef at the bar when I’m back in San Francisco, where his picture is up on the wall. I drink with him for a few minutes before going over to the jukebox. If they still have some of Jef’s picks on there, I choose a song by Lifter Puller. I ask the bartender to turn it up real loud. ●

Isaac Fitzgerald co-hosts AM to DM for BuzzFeed News and is based in New York.